Why Business Structure Matters
Two Freelancers, Different Outcomes:
Alex: Operated as sole proprietor. Client sued for $500,000 over project dispute. Alex's personal assets—savings, home equity—were at risk.
Jordan: Same business, formed LLC. Different client sued. Only business assets at risk. Personal savings, home, retirement protected.
The structure you choose affects:
- Personal liability exposure
- Tax treatment and rates
- Administrative burden
- Credibility with clients
- Exit and scaling options
There's no universally "best" structure. The right choice depends on your business type, income level, risk profile, and goals.
Entity Types Overview
Sole Proprietorship
What it is: You and your business are legally the same. Default for single-person businesses.
Formation: None required. You're automatically a sole prop when you start business activities.
Taxation:
- Business income/loss on Schedule C
- Subject to self-employment tax
- Pass-through to personal return
Liability: None. You're personally liable for all business debts and obligations.
Best for:
- Very small, low-risk businesses
- Testing business ideas
- Low-liability services
- First-year freelancers
Limitations:
- No liability protection
- All income subject to SE tax
- May appear less professional
- Harder to bring on partners
Limited Liability Company (LLC)
What it is: A hybrid entity providing liability protection with flexible taxation.
Formation:
- File Articles of Organization with state
- Create Operating Agreement (especially multi-member)
- Costs $50-500 depending on state
- Annual fees in many states
Taxation (default):
- Single-member: Disregarded, taxed like sole prop (Schedule C)
- Multi-member: Partnership (Form 1065)
- Can elect S-Corp or C-Corp taxation
Liability:
- Personal assets protected from business liabilities
- Must maintain separation (no commingling funds)
- "Piercing the corporate veil" possible if not properly maintained
Best for:
- Any business with liability concerns
- Freelancers and consultants
- Real estate investments
- Small businesses with growth potential
S-Corporation
What it is: A tax election (not a separate entity type) that can apply to LLCs or corporations.
Formation:
- Form LLC or Corporation first
- File Form 2553 with IRS for S-Corp election
- Meet requirements (US shareholders, one class of stock, etc.)
Taxation:
- Pass-through (no double taxation)
- Must pay "reasonable salary" to owner-employees
- Remaining profit as distributions
- Only salary subject to payroll tax
- This is the main benefit
Liability: Depends on underlying entity (LLC or Corp).
Requirements:
- Reasonable salary must be paid
- Payroll processing required
- More complex returns (Form 1120-S)
- Strict operational requirements
Best for:
- Profitable businesses ($70k+ )
- Owner-operators who want to reduce SE tax
- Service businesses with consistent income
C-Corporation
What it is: A separate legal entity, distinct from owners.
Formation:
- File Articles of Incorporation with state
- Create bylaws
- Issue stock
- Hold organizational meeting
Taxation:
- Entity pays corporate tax (21% federal)
- Dividends taxed again to shareholders (double taxation)
- Can retain earnings at corporate rate
- More deduction options
Liability: Strong protection; shareholders not personally liable.
Best for:
- Venture-backed startups
- Businesses planning to go public
- Companies retaining significant earnings
- Situations where double taxation isn't an issue
Comparing Structures
| Feature | Sole Prop | LLC | S-Corp | C-Corp |
|---|---|---|---|---|
| Liability Protection | None | Yes | Yes | Yes |
| Formation Cost | None | Low | Low-Med | Medium |
| Ongoing Complexity | Very Low | Low | Medium | High |
| Self-Employment Tax | Full | Full* | Reduced | N/A |
| Double Taxation | No | No | No | Yes |
| Ownership Flexibility | N/A | High | Limited | High |
| Investment Attractiveness | Low | Medium | Medium | High |
*Unless S-Corp election made
The S-Corp Tax Advantage
How It Works
Without S-Corp (Sole Prop or default LLC):
- $150,000 net profit
- All $150,000 subject to self-employment tax (15.3%)
- SE tax: ~$21,000
With S-Corp election:
- $150,000 net profit
- Pay $80,000 as salary
- $70,000 as S-Corp distribution
- Payroll tax only on salary: ~$12,200
- Savings: ~$8,800
Watch Out
The "reasonable salary" requirement: IRS requires owner-employees take reasonable compensation. Can't pay $10,000 salary and $140,000 distribution. Must reflect market rate for your work.
Audits focus on this. Underpaying salary is a red flag.
When S-Corp Makes Sense
Consider S-Corp when:
- Net profit exceeds $70,000-100,000
- Business is stable with predictable income
- You're comfortable with payroll administration
- Tax savings exceed additional costs
Don't rush into S-Corp if:
- Income is uncertain
- Just starting out
- Profit below $50,000
- Hate administrative complexity
S-Corp Costs and Requirements
Ongoing costs:
- Payroll service: $500-2,000/year
- Tax return preparation: $800-2,500/year
- Possible bookkeeping: $2,400-6,000/year
Requirements:
- Run payroll (at least for yourself)
- File Form 1120-S annually
- Maintain corporate formalities
- Reasonable salary documentation
Break-even analysis: If S-Corp costs $3,000/year extra but saves $8,000 in taxes, it makes sense.
Making the Decision
Year 1: Start Simple
For most new businesses:
- Start as sole proprietor
- Open business bank account
- Track income and expenses
- File Schedule C
Why:
- No upfront cost
- See if business is viable
- Can always form LLC later
- Learn the basics first
When to Form LLC
Form LLC when:
- Business generates consistent income
- You have liability concerns
- Working with clients who expect it
- Have assets worth protecting
LLC formation process:
- Choose state (usually where you live/operate)
- File Articles of Organization
- Get EIN from IRS
- Create Operating Agreement
- Open business bank account
Cost: $50-500 + possible registered agent ($50-150/year)
When to Elect S-Corp
Elect S-Corp when:
- Net profit consistently $70k+
- Understand payroll requirements
- Have accountant to help navigate
- Ready for additional administration
S-Corp election process:
- Have LLC or Corporation in place
- File Form 2553 with IRS
- Can be done by March 15 for current year
- Or within 75 days of entity formation
When to Consider C-Corp
C-Corp makes sense for:
- Seeking venture capital
- Planning IPO
- Want to retain significant earnings at lower rate
- Complex ownership structures
For most small businesses, C-Corp is overkill.
State Considerations
Formation State
Generally form in your home state:
- Where you operate
- Where you live
- Avoid complications
Delaware/Nevada/Wyoming:
- Often advertised for privacy/protection
- Usually not worth it for small business
- May have to register in home state anyway
- Just adds cost and complexity
State Taxes
Be aware of:
- State income tax on business
- Franchise taxes
- Annual report fees
- Sales tax obligations
California example:
- $800 minimum franchise tax for LLCs
- Adds to cost analysis
Multi-Member Considerations
Partnerships
When you have partners:
- Operating agreement is CRITICAL
- Define profit sharing
- Define decision-making
- Define exit procedures
- Get a lawyer involved
Partnership taxation:
- Pass-through to partners
- Each partner gets K-1
- Each pays taxes on their share
Protecting Relationships
Watch Out
Most business partnerships end badly.
Reasons:
- Different visions
- Different work ethics
- Money disputes
- Life changes
Protect yourself:
- Written operating agreement
- Buy-sell provisions
- Clear roles and compensation
- Exit procedures
Working with Professionals
When to Involve a Lawyer
Get legal help for:
- Multi-member LLC formation
- Operating agreement drafting
- Partnership agreements
- Contract review
- Any liability concerns
Cost: $500-2,500 for LLC formation with operating agreement
When to Involve an Accountant
Get accounting help for:
- S-Corp election decision
- Reasonable salary determination
- Tax planning strategies
- Annual filing
Cost: $500-2,500 for election analysis and filing
DIY vs. Professional Formation
DIY may work for:
- Single-member LLC
- Simple business
- Willing to research
- Low-risk situation
Use a professional for:
- Partners involved
- Significant assets
- Liability concerns
- S-Corp election
- Any uncertainty
Common Mistakes
Mistake 1: Choosing Based on Name
"I need an Inc. to look professional." Reality: LLC is fine for 99% of small businesses.
Mistake 2: S-Corp Too Early
"I want to save on taxes from day one." Reality: Costs may exceed savings at low income.
Mistake 3: Delaware for No Reason
"I heard Delaware is best for businesses." Reality: Usually just adds cost for small businesses.
Mistake 4: Ignoring Ongoing Requirements
Forming entity but not maintaining it properly. Reality: Can lose liability protection.
Mistake 5: No Operating Agreement
Multi-member LLC without written agreement. Reality: Recipe for disaster when disagreements arise.
Entity Selection Flowchart
Do This
Decision framework:
-
Are you just starting out? → Start as sole prop, form LLC when stable
-
Do you have liability concerns or assets to protect? → Form LLC
-
Is net profit consistently >$70k? → Consider S-Corp election
-
Do you have partners? → LLC with operating agreement (lawyer involved)
-
Seeking venture capital? → C-Corp likely required
-
None of the above? → Sole prop or single-member LLC is probably fine
The Bottom Line
Start simple—most businesses should begin as sole proprietorships. Form an LLC when you have consistent income and assets worth protecting. Consider S-Corp election when profit exceeds $70k and savings outweigh administrative costs. C-Corp is rarely needed for small businesses. Whatever you choose, maintain proper separation between personal and business finances to preserve liability protection. Work with professionals for complex situations, partnerships, and S-Corp elections. The right structure balances protection, tax efficiency, and administrative burden for your specific situation.
